#138 The Exit: Selling LearnVest for $375 Million

Today on the show! We’re back with The Exit. Where I interview founders after they’ve accomplished the dream. What’s it like to sell the thing you’ve poured your life into for hundreds of millions of dollars?

Here we go!

Today on the show How Alexa Von Tobel, started scaled and… wait a minute… timeout, timeout!

I don’t usually like to toot my own, but I will. Season 11 of The Pitch, this season, was straight fire. If you missed even one episode, you likely missed an incredible pitch.

It started with Nectir raising $1.4 Million on episode 127, and then pitch after pitch, was just deal after deal. Founders raised $2.2 million in the pitch room, and over $2.4M from listeners after the show. And that’s just what we could track. Some of y'all be investing directly without letting me make the intro. Tisk tisk. 

Actually… if you are one of those people who invested in a startup featured on this show, I want to talk with you. We’re building something new. Just for accredited investors, family offices and VCs. I want to give you private access to invest directly into our startups, months before they appear on the show. If this sounds interesting to you, let’s jump on a call. My phone number is 941… jk jk you can email me josh@thepitch.show.

Okay, now it’s time for The Exit.

Today, the woman who started building fintech before fintech was cool. How Alexa von Tobel started, scaled and sold Learnvest for $375 million.

I’m Josh Muccio. On The Pitch, real startup founders pitch real investors for real money. And on The Exit, we tell the rest of the story. Here we go!

Alexa: So if you have tons of money, literally, people are running after you to give you advice. When you have no money, nobody talks to you at all about your money. 

Josh: How do you actually raise the money to kick off the business? 

Alex: People were incredibly skeptical of this idea that in the rearview mirror seemed so stupidly obvious. In fact, it's uncool how obvious it is in the rearview mirror. 

Josh: Yeah, robo advisors. It's an entire category. 

Josh: So you leave Tech Crunch and you launch the business? 

Alexa: Thousands upon thousands of people signed up 

Alexa: And I was like, look at this data. They want this. This is not just me having a gut instinct. This is real. 

Josh: Was it always just up and to the right? 

Alexa: No. God, no. 

Alexa: I earned every wrinkle because it was just good old fashioned hard work. 

Josh: How do you negotiate those term sheets?

Alexa: This has nothing to do with me, my job is to go and be a steward of the company 

Josh: Do you have any regrets about selling LearnVest when you did? 

Our exit interview with Alexa von Tobel is coming up after this. And if you’re not following the show already, subscribe to The Pitch on the Castro podcast app. It’s our favorite place to listen.

[BREAK]

Welcome back. Alexa von Tobel was one of those people who was always going to be an entrepreneur. As a kid, she would take art off the wall of her house and try to sell it on the street. Her parents did not care for that business model. But the enterprising gene was there. Alexa was born where all great entrepreneurs are born – Kentucky!

Alexa: I am like a true, proper southern gal I can easily switch into my accent. I won't. Um, but I'm like, y'all come on over on the front porch. We're gonna serve some lemonade. 

Alexa: Um, very southern. Uh I grew up in Jacksonville, Florida. My dad ran a private practice focused on behavioral disorders, my mom was a developmental pediatric nurse practitioner. And I also worked in my dad's office when I was 8, 9, 10, 11, I spent all of those summers in my dad's office and actually like had a job 

Josh: Yeah Was money something that your family talked about when you were a kid?

Alexa: So my dad, I remember, so I was working at his office, and he opened my first IRA and he was like, this is Your paycheck and here is where it's going. It's going into this IRA and then we would look at the statement and I had this moment where I was like, wow, cool. Like my work is growing and now it's like even when I'm not working, it's still growing. 

Josh: Yeah. 

Alexa: So money was very practical. It was on the table. It was something we could talk about. and it just stuck with me in a really big way 

Josh: Was it that that really got you thinking about money and personal finance as a kid? 

Alexa: No. What really got me thinking about personal finance as a kid is, um, so my dad passed away unexpectedly when I was 14. And I remember very clearly my mom, the sort of family finances were split. My mom bought everything. She was the budgeter. She bought the groceries, the clothes, every stitch of anything that was in our house And my dad managed the investments and insurance and bigger financial topics. And when my dad passed away, I very, very clearly remember. My mom, overnight, being like, Oh my God, I have to like, go figure out all of our finances. that felt very destabilizing, as a 14 year old being like, Oh my God, like, how we manage everything and pay for everything my mom's gotta go learn about right now. That's nuts. and Josh, I won't geek out on you, but there's so much history of why, right? Women couldn't have a credit card they couldn't own land. Like women didn't touch money for most of this last century And so when I got to college, I was like, I am going to learn about personal finance. I'm going to learn about it. I'm going to be good at it.

Josh: Yeah. 

Alexa: And there was no class. And I just remember being like, this is nuts. How? Is there no education here? 

Josh: When you searched online, could you at least find some resources there to get you started?

Alexa: Well, so I graduated from Harvard in 2006. Google existed, but it wasn't Google. There wasn't trusted places to go and get this content all these things we kind of take for granted weren't really there.

Josh: Yeah 

Alexa: in my mind, it was like an ethical pain point. And it's something that really felt like an injustice and got under my skin. right now, 80% of the country lives paycheck to paycheck. And money is your lifeline. It's how you pay for food, shelter, all the things But if you have a lot of money, the wealth advisory space really wants to help you. So if you have tons of money, literally, people are running after you to give you advice. 

Josh: Yeah 

Alexa: When you have no money, nobody talks to you at all about your money. And the more you learn about money, the more you realize it is very damning. It is a category where if you make mistakes, if you hurt your credit score, it's hurt for seven years. If you don't start saving for retirement, it's very hard to catch up later. If you don't have insurance and a catastrophe happens, you go bankrupt. 

Josh: It can destroy you financially

Alexa: it can destroy you. So there's no room for mistakes, yet you have absolutely nobody to give you advice. And I was just like, this is so profoundly stupid. This problem is so profoundly stupid. And what if we could fix it? 

Josh: Yeah. When you saw this need in college, were you immediately thinking, I'm going to start a business? I'm going to try to solve this problem. 

Alexa: I knew I wanted to solve this problem and I didn't quite know what that meant it was, I knew I was entrepreneurial, but starting a company wasn't a thing. It wasn't a career path that was in any way popular, but not even like known, if that makes sense.

So when Alexa graduated from college, she did the usual thing a Harvard grad does – get a job at the Morgan Stanley trading desk. But she couldn’t get this problem out of her mind. 

So on nights and weekends after work, Alexa started writing a business plan for what would eventually become Learnvest. A company that would help young people manage their finances online. 

She went back to Harvard for her MBA in 2008. But Alexa realized pretty quickly that she didn’t really want to be there. She wanted to build Learnvest instead.

Josh: You dropped out in 2008? 

Alexa: my last day was December 18th of 2008 Lehman Brothers went under. The world was in free fall financially and I, and I kind of said to myself, when the world zigs, you have to zag. and I was like, I'm gonna go start a company. I'm gonna move to New York. I'm, I'm sole founder by the way, so I - 

Josh: Oh my gosh, you're crazy, Alexa. 

Alexa: And people were like you're nuts. Why are you doing this? You have a perfect resume. You, you have all this amazingness happening. You're throwing it all away. And I kind of had just said to myself, there was this Harvard study, um, happiness study in a happiness lab that I learned about that kind of really changed my life. Where it's like, when you're 90, you regret not what you do, you regret what you don't do. And it's really that simple. You don't regret the boy you kissed or the stupid thing you did. You don't, you don't remember any of it. You clearly regret the swings you don't take.

Josh: Hm

ALexa: And so I had 90 year old Alexa sitting on my shoulder and she was like, you're gonna be really bummed if you don't go try to build this company. It's been in, it's been in your heart and your head for five years now really. It's time. So I dropped out. Moved to New York. Threw my life upside down. Cried the entire plane ride to New York. Didn't even move out of my dorm because I didn't have the emotional capacity to do one more thing. 

Josh: Wait, you left your stuff?

Alexa: I literally left my stuff 

Josh: To this day, it's still there.

Alexa: No, no, I just left it. 

Josh: There's a shrine 

Alexa: No, I literally, I left all my stuff and I basically, at that point, effectively moved in with my boyfriend, and his amazing roommate, George, and said I've now done the hard thing, I've officially dropped out, I can't go back, the door was closed, I gotta go build this company.

With a business plan, a laptop, and a dream, Alexa got to work. That’s coming up after the break

[BREAK]

Welcome back. Alexa von Tobel dropped out of Harvard Business School in 2008 and moved to New York with a business plan and … not much else. But Alexa remembers that first day at “work” being pretty magical.

Alexa: I opened my laptop, the piece of paper in front of me was blank. And I just had this incredible productivity. And I remember one day of working full time at my own thing with no noise I accomplished more in that one day than I had in the three months prior. plugging in to my purpose, it created this incredible calm. I was starting the most boring company on the planet. Josh, truly I would go to a cocktail party and I would be like, I'm starting a company to help you manage your money. And people would just like turn and keep walking and I had to be like, Let's just not talk about what I'm doing. Like one day it'll maybe work out, but like right now -

Josh: There is that stigma about money. People don't want to talk about it. 

Alexa: Correct. And what I was doing was early. FinTech wasn't even a category. At the time, people were like, you're building a what? I'm like, a FinTech company, finance on the internet. It was just, I mean, it was laughably stupid how boring what I was starting was. 

Josh: Do you go out and pitch investors? Do you go out to Silicon Valley? Like, how do you actually raise the money to kick off the business? 

Alexa: It was New York City. It was 2008 there was New York Angels, which would invest 25,000 to 50,000. And I was thrilled they invested, but an engineer was still, you know, 5,000 to 8,000 a month 

Josh: So it gets you a quarter of an engineer. 

Alexa: It got me nowhere, um, and a lot of the great funds that exist in New York didn't really exist then. Or if they did, they backed the next round. So I was like, how do I get capital for the next round if I can't exist today? 

Josh: Right. 

Alexa: It was like a real pickle. 

Josh: What did that pitch sound like? 

Alexa: So the pitch was, We're going to take a next entire generation and, and be their wealth manager. We are going to do it all online. It's going to be all digital. It's going to be seamless. it's going to be transparent. We're going to be open 24 hours a day. Josh, that sounds dumb. Banks were open 9 to 5.

Josh: Yep. 

Alexa: How on earth am I managing my finances if it's only open during working hours, I have to leave my job. I can't leave my job in the middle of my job to go get access to advice. And so we were like, we're going to be open 24 hours a day. And you paid a subscription service 

Josh: How many people do you think you pitched? 

Alexa: I couldn't tell you because I blacked it all out, Josh, because it was so dramatic and so hard. I mean, my husband, he would come in back to his apartment where I was sitting on the couch and I would sometimes just have like tears coming down my cheeks, but I was just still working. It was a nightmare. I was so demoralized, Josh. Because like, so many no's came through. Be like, no, no, no, no. and then I'd come home and it'd be a little yes and he was like we would celebrate it like the Giants have won the Super Bowl. My husband's a huge Giants fan Um, I would be like, yes, we raised $10,000 and and then it'd be like we raised a hundred thousand dollars today. 

Josh: Yeah

Alexa: and It just started to move, right? momentum is real. It is massive 

Josh: I mean, how long did it take to close that first round?

Alexa: Uh, from January 1st of 2009 to September of 2009. So nine months So our first capital round outside of my own dollars was $1.1 million. 

Josh: Do you remember what the terms of that initial million were? 

Alexa: It was a true pre-seed round. basically sub $10 million, valuation. And I just remember being like, I'm in business. 

Josh: This is real now. 

Alexa: This is real. 

Josh: Yeah. If you were to go back and tell yourself at the beginning of that fundraising process, one tip What would it have been? 

Alexa: find the five smartest people you know and let them shred your company. it sucks for somebody to be like, this is a terrible idea. This part sucks. This part sucks but I think that the thing that I wish I would have told myself is like Really lean into the negative feedback, because that's, those are the questions you have to answer, those are the questions you need to know. when three of the same smart people say the same piece of feedback, it's probably real feedback. 

Josh: So, you've got a million dollars, the business is capitalized, what did you do next?

Alexa: Well, I went to TechCrunch50 now it's I think called TechCrunch Disrupt, but back then they picked the 50 biggest, brightest ideas in the country, brought everybody together, And I got up to pitch my idea to a live audience. I think there was probably 1,500 people in the audience. 

Josh: Yeah. 

Alexa: And I present my idea to a panel of four guys. And they were like, why on earth would anyone manage their wallet online? Um, this is a terrible idea. Gamification of the wallet makes no sense. I don't think people want their wallet to have any delightful reward. 

Josh: Get out. They couldn't be more wrong. 

Alexa: And I, in that moment, was so calm. And I was like, let me tell you why you're wrong. And ended up getting a standing ovation. I walked off stage, Burst into tears, called my boyfriend, now husband, and was like, I just got tech punched. Like, literally, they shredded me. People were incredibly skeptical of this idea that in the rearview mirror seemed so stupidly obvious. In fact, it's uncool how obvious it is in the rearview mirror. 

Josh: Yeah, robo advisors. It's an entire category. 

Alexa: But at the time, people thought it was stupid. 

Josh: So you leave TechCrunch, um, TechPunch, and you launch the business, off the back of that presentation, yes?

Alexa: Yeah, so we opened our first product, which was January 1st, New Year, New You. And we launched these boot camps for your money, where you could go online, they were free to take And Daily Candy wrote about us And thousands upon thousands of people signed up and I'd taken one day off to go skiing with a bunch of friends. And I'm at the top of the mountain, and I get a phone call that our website has crashed. can't make this stuff up, and I, like, go as fast as I can down the mountain. Almost get a complete concussion. Literally.

Josh: No, really? You fell?

Alexa: Oh, I fully fell. Fully. I had no time to be a great skier. I was like, completely, fall. 

Josh: I just gotta get down this mountain.

Alexa: I just gotta get down this mountain. And anyway, they'd written about us It was the first time I was like, you tech punch people, shut up. Look at this. This is real Men, women, young, old, look at this data. They want this. This is real. This is not just me having a gut instinct. This is real. by the end of the month, we had about 50,000 signups. And what was really crazy is then all of a sudden, I had almost 10 term sheets being like, I want to commit to your Series A. 

Josh: How do you negotiate those term sheets? How do you pick who to let invest in your company? 

Alexa: I went with Excel Venture Partners. The partner there, Teresa made me feel that I, Could just be myself and she just I think really appreciated that I was on a mission and I was not gonna take no for an answer and we were gonna build this company and we're gonna figure it out and what's funny. I also didn't take the highest valuation Because I was like building a business is about getting the right people in the boat and being really thoughtful about the long term

Josh: Yeah 

Alexa: And I just remember to this day. When I told a few people no, who yelled at me. Um, and I remember just being like, I'm a kid, you're a grown up. Why are you yelling at me? 

Josh: Wait wait wait you told them no, I'm not going to let you invest in my company What did they say? 

Alexa: You're making the biggest mistake of your life. This is stupid. What you're doing is stupid. This is terr- 

Josh: Wait, you wanted to invest in me and now you're calling this business stupid.

Alexa: And now you're calling me stupid. and I just remember being like sort of giggling, being like, okay, I got to get back to work. and ended up raising almost 6 million in our Series A 

Josh: Yeah.

Alexa: And with that capital, we started to build TurboTax for financial planning, where we could make and build a financial plan for anybody in America. 

Josh: At this point, financial planning was something that people just trusted to incumbents like Schwab that had been around for a hundred years. What did they think of LearnVest?

Alexa: The one big thing that the incumbents really had is trust, right? When you think of Charles Schwab, when you think of J. P. Morgan first of all, they’re names. They’re names of humans, because trust is human. 

Josh: Yeah. 

Alexa: but they built this incredible trust, so they're really hard to beat. Incumbents are very hard to unseat in FinTech specifically. And what's interesting is LearnVest was doing something that was hard for them to do. we were like, here are our fees, it's extremely transparent. The incumbents, it sort of was an Achilles heel because they couldn't just say, here are our fees up front because they were hidden and it was a big business model change. Secondly, we created a ton of content and we could do it really authentically because we weren't selling any financial products. We just were an advisory platform And so we played to our strengths because we were little. We were the underdog. We thought about, what are our competitive moats that we can execute on that it's hard for them to do. 

Josh: Right, they have all this like legacy baggage that comes with being a brand that's been around for that long.

Alexa: Correct. 

Josh: What was the thing that really caused you to continue to grow sustainably? 

Alexa: It was SEO. It was social. It was refer a friend. It was email newsletters. It was live events. It was press, PR, books, business development partnerships. brand affiliations we would do. It was all of it 

Josh: All of that was key to your success. 

Alexa: All of it. We were running all of it because there wasn't like a secret unfair advantage, if that makes sense. and Josh, we spent nothing on marketing. It wasn't like we had a million dollar a year marketing budget. We spent tens of thousands of dollars, nothing in the rear view mirror to build a user base of millions of users. 

Josh: That’s incredible. 

Alexa: That's Every hack that could exist we were, we were employing. 

Josh: Was it always just up and to the right? 

Alexa: No. God, no. What was amazing about LearnVest was that it was truly a miserably hard company to build 

Josh: What do you mean miserably hard? 

Alexa: So first it was regulated. We were a registered investment advisor. So every piece of content we made had to go through compliance, which just meant like one hand was tied behind your back. 

Josh: Mmm

Alexa: Two, we were going up against incumbents that had incredible trust 

Josh: Larger budgets. 

Alexa: Large budgets. 

Josh: Huge marketing budgets.

Alexa: Massive. We were in New York City, pre the tech. It wasn't like a big tech city, right? So it was like, even finding talent was complicated at times. And then I used to say, God, I want to sell something that people really, really want. And every day I would wake up and be like, no one wakes up and is like, can't wait to get a financial plan. Like we, we had to find people in the moment when they needed it. 

Josh: Right. When there's an emergency.

Alexa: Yep. 

Josh: And they realize how bad their finances are.

Alexa: Everything was hard. There was nothing that came easily. Nothing. I joke, I'm like, I earned every wrinkle. I earned, because it was just good old fashioned hard work.

After four more years of hard work, Alexa had raised 73 million in venture funding. Her last round, the series D, was led by Northwestern Mutual. Yes, the insurance company. And not long after that… Northwestern Mutual came back to the table for a different reason. The exit, coming up after the break.

[BREAK]

Welcome back. Learnvest had just raised their series D from Northwestern Mutual in 2014. But a few months later, they wanted to talk...again. This time, it was the CEO John Schlifske

Alexa: At this point I'm five months pregnant and he's like, what if we teamed up? and what if we did a combination was the word he used and he, he meant like, what if we merged the companies? And I was like, merge, your, you do almost 40 billion of revenue 

Josh: Yeah. What do you mean by merge? 

Alexa: Merge. Yeah. I'm like, you could swallow me. Um, and no, he had this brilliant idea. It was like, what if we teamed up? He was like, your value system, why you get out of bed every day is you want to give more Americans financial plans.

We have a team that can do that That's part of what they do. They give as many plans away as possible and so having a software that made that beautiful and seamless and modern and online and on your phone. 

Josh: Yeah. It just makes sense. 

Alexa: It just makes sense. 

Josh: What was the original offer to buy LearnVest? 

Alexa: We got a term sheet the early days of December and it had a range you know, 300 to four something my board was like, you can't have a range, we need a number. What's the number? So, I got to work, I would run the company during the day and at night would have my second shift of running the acquisition. We went through the next four months of thinking it through and we had some other big acquirers circling and we didn't need to sell. We had 50 million dollars, 50 plus million dollars of cash 

Josh: Oh, just sitting in the bank. 

Alexa: Yup 

Josh: When you finally get the term sheet from them, how did you react when you got it? 

Alexa: I mean, I think I was very, very balanced about all of this. I'm one of these people who's like, nothing is real until it's real. Nothing. 

Josh: Yeah. 

Alexa: Nothing in life is real until it is signed, sealed, and delivered. And so, I was like, my job as CEO. This has nothing to do with me, even though I'm the largest shareholder of the company. My job is to go and be a steward of the company. Like, is this the right thing to do for the company? Is this the right thing to do for the team? I very much like didn't allow myself to have an emotional reaction because I was like, my job is to collect the data. And to put it in a packageable way where everybody can see it. 

Josh: You didn't let yourself react emotionally to an offer over 300 million dollars? 

Alexa: No, because I was like, I have had really good friends have offers completely disintegrate on the finish line. Like, I knew how it could potentially not be real at all. 

Josh: Yeah. What was the back and forth like in your mind? like, what made you want to say yes and maybe what made you want to say no? 

Alexa: What I loved most about the team at Northwestern Mutual was, they sat in a room with us one day. I'm literally at this point, eight and a half months pregnant, where I didn't have a crib, I mean, like, in the back of my head, I'm like, oh my god, I need so many things for this human that I'm about to have and I'm sitting in this room and they were like, we just want to sit in a room together for a day. And just get to know each other It was just the right thing. It's like, businesses are personal. They're about people. People do extraordinary things. People are what make and change the planet, move time and space. And it was just such a beautiful message. And I, I learned so much from how they operate because it's about the people. And they, that's, we sat in a room and we chatted all day at the end, I was like, I really know who these people are. And like, I really am excited to work with them. 

Josh: Was that the moment you were like, all right, we're going to do this? 

Alexa: I actually didn't think about it at all until the morning where both boards said this is officially approved and I had to put my signature on it. We ended up selling for just about three hundred and seventy five million dollars. And the board said, send us a video of how you're feeling. And I took out my my camera and I like just was like, I told them that. A Northwestern mutual life insurance policy is what stabilized my family when my dad passed away.

Josh: Oh my god.

Alexa: And I'd not told a soul, I'd not told them the whole time. And I said, I think this is what I'm meant to do with this business that I care so much about and I literally know the value of what their product does for a family going through extreme stress and trauma. And I was like, this is what I was meant to do with the business. it still gives me goosebumps. It was exactly what I was supposed to do. 

Josh: That's incredible that they paid the life insurance policy for your dad. That's wild. And they didn't, know until after the deal was done and you told them.

Alexa: Nobody knew. The only person who knew was my husband. 

Josh: Yeah 

Alexa: But it was, to my bones, I knew I was doing the right thing I just knew it was not an accident 

Josh: Yeah

Alexa: I was supposed to stay for three years, I stayed four 

Josh: After the sale? 

Alexa: After the sale, and I said to them, I am here to be the teammate in every way, because I, like, deeply bleed blue. This company is a really special one. 

Josh: So you stuck around for four years. You still speak very highly of the company, which I just have to say after seeing and speaking to a lot of entrepreneurs, that's really rare. Like everybody has the best of hopes going into it. Everybody believes that this acquisition is the right thing to do. Like everybody says those things and everybody feels like the acquirer has their best interests in mind. But then you get into the details afterwards of assimilating these two companies and things just aren't the same So it's surprising to me to hear you say it was good. 

Alexa: I absolutely knew this was going to be very hard Any two companies, two cultures, you can look almost as similar as somebody else as humanly possible and it's still hard. And so it was really hard at times, right? Tiny tech company in New York that runs fast and breaks things. 

Josh: Yeah. 

Alexa: Life insurance company that is so stable. They break nothing, truly that is the job. 

Josh: Yeah. 

Alexa: No breaking 

Josh: Yeah, I imagine the culture's a bit different.

Alexa: Yeah, when you buy a policy, they have to know that they will be here in 100 years. 

Josh: Right. How did you know when it was time to leave? 

Alexa: You know, it's sort of a hard act to follow because LearnVest wasn't like a company I was trying to build. I wasn't like, let's go be a successful entrepreneur. I was on a mission. There was something like deep in my heart and I'd been actively angel investing and investing, while I was at Northwestern Mutual. And I, I felt this thing become alive in me again and I kind of know myself really well. I know when. I'm being activated, and I had this bone to pick with Venture, you know, I'd flipped my life upside down, I'd move to New York City, and I was like, where is the capital that is meeting me? I want to go build the fund for those entrepreneurs where they are on a mission. It is their life's work. They are changing the world. there's an injustice they want to disrupt. There is a societal problem that they think they can make a dent in. And then you want really patient capital to just sit there and be their teammate all the way through. And it literally, I was sitting still and I was like, I just want inspired capital. And then I was like, Inspired Capital, is the name taken? And of course the name is going to be taken, it's called Inspired.

Josh: Yeah

Alexa: Name wasn't taken. 

Josh: Wow.

Alexa: And literally, we bought it and the next day I told my mom, I was like, Mom, I'm starting a new company, this is what it's going to be. Started making phone calls and I felt myself like become a kid again. I was like. I, I'm a kid in a candy store. This is my next chapter. And my husband was like, do you want to think about this for a minute? And I was like, no, there's nothing to think about. This is it. 

Josh: So you just, you put in your notice right away and you started Inspired Capital. 

Alexa: Like literally the next day.

Josh: That's amazing. So fast. So You guys are on fund two now, is this correct? 

Alexa: Yep, we're on fund two. 

Josh: 281 million dollar fund. Apparently you raised it in six weeks, which is insane. 

Alexa: Yeah, I mean, it was wonderful. I was customer number one in building the venture fund that I wish existed when I was a 24, 25 year old dropout.

Josh: Yeah. 

Alexa: Where I knew how I felt, I knew how I wanted somebody to make me feel. 

Josh: Do you have any regrets about selling LearnVest when you did? 

Alexa: No regrets. no, life is too short for regrets. No

Josh: So, like, you don't even allow mental space to think about whether you'd regret something.

Alexa: No, no. Life is too short to rewind. Coulda, woulda, shoulda is a waste of brain cells. it was the most authentically right thing for me to do. Period. It's that simple. Somebody once said to me, like, do what you love to do, and you'll never work a day in your life, and I, I've actually come up with this one, which is, um, Do what you love, and you will work every day of your life, all the time, with no boundaries, and take things extremely personally, because you care so much.

Alright, my sweet, sweet pitchlings. That brings us to the end of season 11. I hope you loved this season. If you did, tell a friend! That’s the best thing you can do to help our show. Season 12 will be here before you can say EBITDA. No but for real, we’ll be back at a date and a time.

Until then, you can go to patreon.com/thepitch. We’re dropping previously unreleased uncut pitches from our Miami event. See you over there <3

This episode was made by me, Josh Muccio, Lisa Muccio, Anna Ladd, Enoch Kim, and Jackie Papanier.

Music in this episode is by Breakmaster Cylinder, The Muse Maker, Amico Mio, Meowtastic, Greg Jong, and JB Lucas.

The Pitch is made in partnership with the Vox Media Podcast Network.